#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:36:03 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179118 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/80/4308031.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4308031
loop_
_publ_author_name
'Erwan Galardon'
'Emilie Bourles'
'Isabelle Artaud'
'Jean-Claude Daran'
'Pascal Roussel'
'Alain Tomas'
_publ_section_title
;
Metalation of Cyclic Pseudopeptidic Thiosulfinates with Ni(II) and Zn(II)
after Ring Opening: A Mechanistic Investigation
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4515
_journal_page_last               4522
_journal_paper_doi               10.1021/ic062480m
_journal_volume                  46
_journal_year                    2007
_chemical_formula_sum            'C32 H59 N5 Ni O4 S2'
_chemical_formula_weight         700.67
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.830(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.190(2)
_cell_length_b                   11.3450(10)
_cell_length_c                   21.092(2)
_cell_measurement_temperature    120(2)
_cell_volume                     3644.4(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32408
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.688
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1512
_refine_diff_density_max         1.694
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         6225
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.256
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1601
_reflns_number_gt                4596
_reflns_number_total             6225
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic062480m-file001.cif
_cod_data_source_block           erw
_cod_database_code               4308031
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.88383(3) 0.96753(4) 0.12909(3) 0.03207(19) Uani 1 1 d . . .
S1 S 0.75621(7) 0.96099(9) 0.05672(6) 0.0381(3) Uani 1 1 d . . .
S2 S 0.88926(7) 1.15210(10) 0.15065(7) 0.0430(3) Uani 1 1 d . . .
N2 N 0.9933(2) 0.9496(3) 0.19680(19) 0.0359(8) Uani 1 1 d . . .
N1 N 0.8873(2) 0.8037(3) 0.11874(19) 0.0355(8) Uani 1 1 d . . .
O1 O 0.6910(2) 0.9334(3) 0.0897(2) 0.0523(9) Uani 1 1 d . . .
O2 O 0.7253(2) 1.0520(3) 0.0051(2) 0.0539(9) Uani 1 1 d . . .
O3 O 0.8326(2) 0.6378(3) 0.0549(2) 0.0611(10) Uani 1 1 d . . .
O4 O 1.1123(2) 1.0359(3) 0.2771(2) 0.0645(11) Uani 1 1 d . . .
C1 C 0.7679(3) 0.8247(4) 0.0130(2) 0.0360(9) Uani 1 1 d . . .
C2 C 0.8325(3) 0.7460(4) 0.0658(2) 0.0397(10) Uani 1 1 d . . .
C3 C 0.9569(3) 0.7498(4) 0.1704(2) 0.0379(10) Uani 1 1 d . . .
C4 C 0.9710(3) 0.6281(4) 0.1809(3) 0.0517(13) Uani 1 1 d D . .
C5 C 1.0422(4) 0.5898(5) 0.2352(3) 0.0588(14) Uani 1 1 d D . .
C6 C 1.0977(4) 0.6672(5) 0.2782(3) 0.0566(13) Uani 1 1 d D . .
C7 C 1.0855(3) 0.7889(5) 0.2684(3) 0.0464(11) Uani 1 1 d D . .
C8 C 1.0160(3) 0.8314(4) 0.2142(2) 0.0381(10) Uani 1 1 d . . .
C9 C 1.0419(3) 1.0419(4) 0.2293(2) 0.0410(10) Uani 1 1 d . . .
C10 C 1.0053(3) 1.1626(4) 0.2020(3) 0.0437(11) Uani 1 1 d . . .
C11 C 0.8093(3) 0.8574(4) -0.0400(3) 0.0484(11) Uani 1 1 d . . .
H11A H 0.8262 0.7854 -0.0582 0.058 Uiso 1 1 calc R . .
H11B H 0.8614 0.9062 -0.0192 0.058 Uiso 1 1 calc R . .
H11C H 0.7667 0.9015 -0.0766 0.058 Uiso 1 1 calc R . .
C12 C 0.6789(3) 0.7657(4) -0.0202(3) 0.0479(12) Uani 1 1 d D . .
C13 C 1.0151(4) 1.2466(4) 0.2617(3) 0.0612(15) Uani 1 1 d D . .
H13A H 1.0775 1.2609 0.2861 0.073 Uiso 1 1 calc RD . .
H13B H 0.9881 1.2108 0.2922 0.073 Uiso 1 1 calc R . .
H13C H 0.9858 1.3215 0.2446 0.073 Uiso 1 1 calc R . .
C14 C 1.0585(4) 1.2060(7) 0.1595(4) 0.088(2) Uani 1 1 d . . .
H14A H 1.1211 1.2028 0.1862 0.106 Uiso 1 1 calc R . .
H14B H 1.0418 1.2874 0.1454 0.106 Uiso 1 1 calc R . .
H14C H 1.0467 1.1557 0.1196 0.106 Uiso 1 1 calc R . .
N5 N 0.5223(4) 1.2577(5) -0.0344(3) 0.0799(16) Uani 1 1 d . . .
C31 C 0.5209(3) 1.1663(5) -0.0539(3) 0.0573(13) Uani 1 1 d . . .
C32 C 0.5193(4) 1.0470(5) -0.0791(4) 0.081(2) Uani 1 1 d D . .
H32A H 0.5260 1.0491 -0.1235 0.097 Uiso 1 1 calc RD . .
H32B H 0.4632 1.0098 -0.0829 0.097 Uiso 1 1 calc RD . .
H32C H 0.5675 1.0016 -0.0479 0.097 Uiso 1 1 calc RD . .
N3 N 0.6584(2) 0.4266(3) 0.16611(19) 0.0353(8) Uani 1 1 d . . .
C15 C 0.7162(3) 0.4232(4) 0.2396(2) 0.0422(10) Uani 1 1 d D . .
C16 C 0.8122(4) 0.4121(5) 0.2524(3) 0.0552(13) Uani 1 1 d D . .
C17 C 0.6635(3) 0.3115(4) 0.1306(3) 0.0454(11) Uani 1 1 d D . .
C18 C 0.6283(4) 0.2038(4) 0.1558(3) 0.0614(15) Uani 1 1 d D . .
C19 C 0.6872(3) 0.5239(4) 0.1285(3) 0.0450(11) Uani 1 1 d D . .
C20 C 0.6880(4) 0.6451(4) 0.1574(3) 0.0554(13) Uani 1 1 d D . .
C21 C 0.5654(3) 0.4477(4) 0.1649(3) 0.0455(11) Uani 1 1 d D . .
C22 C 0.4959(3) 0.4531(5) 0.0966(3) 0.0600(14) Uani 1 1 d . . .
H22A H 0.5080 0.5191 0.0711 0.072 Uiso 1 1 calc R . .
H22B H 0.4384 0.4643 0.1015 0.072 Uiso 1 1 calc R . .
H22C H 0.4958 0.3793 0.0724 0.072 Uiso 1 1 calc R . .
N4 N 0.1831(2) 0.6977(3) 0.0854(2) 0.0438(9) Uani 1 1 d . . .
C23 C 0.1314(3) 0.7852(5) 0.0327(3) 0.0525(13) Uani 1 1 d . . .
H23A H 0.1683 0.8559 0.0355 0.063 Uiso 1 1 calc R . .
H23B H 0.1198 0.7498 -0.0124 0.063 Uiso 1 1 calc R . .
C24 C 0.0453(4) 0.8237(6) 0.0385(4) 0.0723(18) Uani 1 1 d . . .
H24A H 0.0056 0.7560 0.0309 0.087 Uiso 1 1 calc R . .
H24B H 0.0190 0.8846 0.0048 0.087 Uiso 1 1 calc R . .
H24C H 0.0554 0.8557 0.0837 0.087 Uiso 1 1 calc R . .
C25 C 0.1969(4) 0.7426(5) 0.1554(3) 0.0581(14) Uani 1 1 d D . .
C26 C 0.2321(5) 0.8675(5) 0.1695(4) 0.0679(16) Uani 1 1 d D . .
C27 C 0.1335(3) 0.5826(5) 0.0757(3) 0.0593(14) Uani 1 1 d D . .
H27A H 0.0771 0.5967 0.0831 0.071 Uiso 1 1 calc RD . .
H27B H 0.1196 0.5574 0.0283 0.071 Uiso 1 1 calc R . .
C28 C 0.1803(4) 0.4834(5) 0.1208(4) 0.0734(18) Uani 1 1 d . . .
H28A H 0.2358 0.4670 0.1134 0.088 Uiso 1 1 calc R . .
H28B H 0.1433 0.4127 0.1104 0.088 Uiso 1 1 calc R . .
H28C H 0.1924 0.5056 0.1680 0.088 Uiso 1 1 calc R . .
C29 C 0.2723(3) 0.6804(4) 0.0775(3) 0.0452(11) Uani 1 1 d D . .
C30 C 0.2696(3) 0.6225(5) 0.0130(3) 0.0543(13) Uani 1 1 d . . .
H30A H 0.2458 0.5427 0.0110 0.065 Uiso 1 1 calc R . .
H30B H 0.3292 0.6185 0.0110 0.065 Uiso 1 1 calc R . .
H30C H 0.2322 0.6686 -0.0253 0.065 Uiso 1 1 calc R . .
H4 H 0.924(3) 0.575(5) 0.146(3) 0.08(2) Uiso 1 1 d D . .
H5 H 1.051(5) 0.5036(15) 0.244(4) 0.099 Uiso 1 1 d D . .
H6 H 1.156(3) 0.641(5) 0.324(2) 0.080(19) Uiso 1 1 d D . .
H7 H 1.119(4) 0.851(4) 0.301(3) 0.08(2) Uiso 1 1 d D . .
H12A H 0.653(5) 0.754(6) 0.015(3) 0.096 Uiso 1 1 d D . .
H12B H 0.696(5) 0.696(4) -0.039(3) 0.096 Uiso 1 1 d D . .
H12C H 0.643(4) 0.823(5) -0.055(3) 0.096 Uiso 1 1 d D . .
H15A H 0.688(4) 0.364(4) 0.256(4) 0.096 Uiso 1 1 d D . .
H15B H 0.694(5) 0.494(4) 0.259(4) 0.096 Uiso 1 1 d D . .
H16A H 0.837(5) 0.478(4) 0.238(4) 0.096 Uiso 1 1 d D . .
H16B H 0.840(4) 0.401(6) 0.3040(7) 0.096 Uiso 1 1 d D . .
H16C H 0.826(5) 0.342(4) 0.226(3) 0.096 Uiso 1 1 d D . .
H17A H 0.7234(15) 0.311(6) 0.134(4) 0.096 Uiso 1 1 d D . .
H17B H 0.623(4) 0.330(6) 0.0754(11) 0.096 Uiso 1 1 d D . .
H18A H 0.5589(7) 0.206(6) 0.141(4) 0.096 Uiso 1 1 d D . .
H18B H 0.643(5) 0.132(4) 0.129(3) 0.096 Uiso 1 1 d D . .
H18C H 0.660(4) 0.199(6) 0.2114(6) 0.096 Uiso 1 1 d D . .
H19A H 0.743(2) 0.505(6) 0.129(4) 0.096 Uiso 1 1 d D . .
H19B H 0.638(3) 0.515(6) 0.0775(15) 0.096 Uiso 1 1 d D . .
H20A H 0.713(4) 0.697(5) 0.125(3) 0.096 Uiso 1 1 d D . .
H20B H 0.631(2) 0.672(6) 0.155(4) 0.096 Uiso 1 1 d D . .
H20C H 0.721(4) 0.643(6) 0.2036(9) 0.096 Uiso 1 1 d D . .
H21A H 0.555(5) 0.381(4) 0.189(3) 0.096 Uiso 1 1 d D . .
H21B H 0.570(5) 0.522(4) 0.192(3) 0.096 Uiso 1 1 d D . .
H25A H 0.138(2) 0.747(6) 0.161(4) 0.096 Uiso 1 1 d D . .
H25B H 0.240(4) 0.681(5) 0.183(3) 0.096 Uiso 1 1 d D . .
H26A H 0.244(5) 0.885(6) 0.2176(10) 0.096 Uiso 1 1 d D . .
H26B H 0.183(3) 0.920(5) 0.137(3) 0.096 Uiso 1 1 d D . .
H26C H 0.2969(19) 0.879(6) 0.169(4) 0.096 Uiso 1 1 d D . .
H29A H 0.310(4) 0.643(6) 0.116(2) 0.096 Uiso 1 1 d D . .
H29B H 0.297(4) 0.761(3) 0.078(4) 0.096 Uiso 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ni1 N1 85.58(15) . . ?
N2 Ni1 S1 171.09(11) . . ?
N1 Ni1 S1 86.66(11) . . ?
N2 Ni1 S2 89.10(11) . . ?
N1 Ni1 S2 174.31(12) . . ?
S1 Ni1 S2 98.49(5) . . ?
O2 S1 O1 112.4(2) . . ?
O2 S1 C1 106.7(2) . . ?
O1 S1 C1 105.56(19) . . ?
O2 S1 Ni1 121.19(15) . . ?
O1 S1 Ni1 110.23(17) . . ?
C1 S1 Ni1 98.63(14) . . ?
C10 S2 Ni1 98.62(15) . . ?
C9 N2 C8 123.5(4) . . ?
C9 N2 Ni1 122.8(3) . . ?
C8 N2 Ni1 113.5(3) . . ?
C2 N1 C3 124.2(4) . . ?
C2 N1 Ni1 123.0(3) . . ?
C3 N1 Ni1 112.8(3) . . ?
C12 C1 C2 112.6(4) . . ?
C12 C1 C11 110.5(4) . . ?
C2 C1 C11 108.2(4) . . ?
C12 C1 S1 110.9(3) . . ?
C2 C1 S1 106.6(3) . . ?
C11 C1 S1 107.9(3) . . ?
O3 C2 N1 126.3(4) . . ?
O3 C2 C1 118.8(4) . . ?
N1 C2 C1 114.8(4) . . ?
C4 C3 N1 126.3(4) . . ?
C4 C3 C8 119.9(4) . . ?
N1 C3 C8 113.8(4) . . ?
C5 C4 C3 118.9(5) . . ?
C6 C5 C4 121.5(5) . . ?
C5 C6 C7 120.7(5) . . ?
C8 C7 C6 119.9(5) . . ?
C7 C8 N2 127.8(4) . . ?
C7 C8 C3 119.2(4) . . ?
N2 C8 C3 113.0(4) . . ?
O4 C9 N2 125.9(4) . . ?
O4 C9 C10 119.2(4) . . ?
N2 C9 C10 114.9(4) . . ?
C14 C10 C9 106.7(5) . . ?
C14 C10 C13 111.0(5) . . ?
C9 C10 C13 109.2(4) . . ?
C14 C10 S2 110.2(4) . . ?
C9 C10 S2 110.8(3) . . ?
C13 C10 S2 108.9(4) . . ?
N5 C31 C32 179.8(9) . . ?
C15 N3 C21 106.6(4) . . ?
C15 N3 C17 111.4(3) . . ?
C21 N3 C17 110.3(3) . . ?
C15 N3 C19 111.1(3) . . ?
C21 N3 C19 110.8(4) . . ?
C17 N3 C19 106.7(3) . . ?
C16 C15 N3 115.5(4) . . ?
C18 C17 N3 115.4(4) . . ?
C20 C19 N3 114.4(4) . . ?
C22 C21 N3 116.1(4) . . ?
C25 N4 C27 108.7(4) . . ?
C25 N4 C23 111.1(4) . . ?
C27 N4 C23 109.4(4) . . ?
C25 N4 C29 108.7(4) . . ?
C27 N4 C29 110.8(4) . . ?
C23 N4 C29 108.2(3) . . ?
C24 C23 N4 115.3(4) . . ?
N4 C25 C26 115.4(5) . . ?
C28 C27 N4 115.6(5) . . ?
C30 C29 N4 114.8(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N2 1.873(4) . ?
Ni1 N1 1.875(3) . ?
Ni1 S1 2.1129(13) . ?
Ni1 S2 2.1382(12) . ?
S1 O2 1.460(4) . ?
S1 O1 1.482(3) . ?
S1 C1 1.843(4) . ?
S2 C10 1.826(5) . ?
N2 C9 1.348(6) . ?
N2 C8 1.406(6) . ?
N1 C2 1.338(6) . ?
N1 C3 1.413(6) . ?
O3 C2 1.250(5) . ?
O4 C9 1.241(6) . ?
C1 C12 1.525(6) . ?
C1 C2 1.530(6) . ?
C1 C11 1.531(6) . ?
C3 C4 1.405(6) . ?
C3 C8 1.424(6) . ?
C4 C5 1.390(8) . ?
C5 C6 1.360(9) . ?
C6 C7 1.400(7) . ?
C7 C8 1.390(7) . ?
C9 C10 1.525(7) . ?
C10 C14 1.520(7) . ?
C10 C13 1.543(7) . ?
N5 C31 1.112(7) . ?
C31 C32 1.451(8) . ?
N3 C15 1.515(6) . ?
N3 C21 1.516(5) . ?
N3 C17 1.521(5) . ?
N3 C19 1.522(5) . ?
C15 C16 1.491(7) . ?
C17 C18 1.519(7) . ?
C19 C20 1.503(7) . ?
C21 C22 1.498(8) . ?
N4 C25 1.504(7) . ?
N4 C27 1.509(6) . ?
N4 C23 1.513(6) . ?
N4 C29 1.521(6) . ?
C23 C24 1.505(7) . ?
C25 C26 1.519(9) . ?
C27 C28 1.503(8) . ?
C29 C30 1.499(7) . ?
